Thaddeus Jimenez. Jimenez won a $25 million award in 2012 for a wrongful murder conviction only to spend it on rebuilding his Simon City Royals street gang and committing new crimes

A Chicago gang member who received $25million in a wrongful conviction judgement and was freed from prison after serving 16 years for a crime he didn't commit is headed back behind bars after he spent all of his money and randomly shot a friend in both legs.

Gang member Thaddeus Jimenez, 37, who ran the Simon City Royals gang in Chicago, was sentenced to nine years in prison on Thursday for shooting an acquaintance in the knees.

Jimenez, who had been introduced to the gang life early thanks to his uncles, had been wrongfully convicted in a gang murder in 1997 when he was 13, tried as an adult, and sentenced to 45 years in prison, reported the Chicago Tribune.

Jimenez sued the city and the police department and in 2012, a federal jury awarded him $25million, one of largest police misconduct awards in city history.

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After being released from prison, Jimenez went back to his old gang ways, and financed the reboot of his old gang, Simon City Royals - he would give cash bonuses to those who would get the gang's insignia tattooed on their faces, like he had

In 2015, he and a fellow gang member filmed themselves shooting an acquaintance, Earl Casteel, 33, whom they happened to meet on the street.

On Thursday, the judge sentenced him to nine years after viewing the video.

Jimenez was serving his time for a crime he didn't commit when his luck turned. After years of begging legal advocates to look at his case, attorneys and students from the Northwestern University Bluhm Center on Wrongful Convictions agreed to do so.

Jimenez, above, at 13 (left) and 12 (right), the age he was when he was convicted as an adult for killing a gang member he didn't kill, he served 16 years

His advocates found proof that another man had confessed to the murder that Jimenez was convicted of, two key witnesses recanted their earlier statements, and a judge acquitted Jimenez in 2007.

He had served 16 years behind bars, often in solitary confinement, one time having little contact with other people for four years. Because of his small stature, he was often beaten in prison.

When he was released, his old gang, Simon City Royals, was basically defunct. Instead of living a life of leisure, or giving back to the community, Jimenez decided to recruit get his old gang back together, and terrorize the community around their 'turf' on Irving Park.

Attorney Jon Loevy, left, with his client Thaddeus Jimenez, who was arrested at 13 only to be exonerated after serving 16 years in prison

Jimenez and Roman were in this black convertible Mercedes when they shot Casteel - they then took off and crashed it

Jimenez, according to the Chicago Tribune, spent virtually all of his fortune (after lawyers took their half) on cars, guns, recruiting new gang members with cash, and giving cash bonuses to those who would tattoo the crew's insignia on their faces. He would also bail members out of prison.

New gang members could make $50,000. He once bailed out a member for $100,000.

Jimenez (in red hat) and fellow gang member Roman drove around Irving Park area until they saw a man they knew, Earl Casteel (above in the black t-shirt)

'What's up, folks?' asks an oblivious Casteel who approached the car

'Why shouldn't I blast you right now' Jimenez demands of an astonished Casteel, who thinks they're friends

Jimenez is seen shooting Casteel in the legs and, as the man screams in pain, driving away

'His new family became the gang, reconstructed from his childhood memory of his uncles [who introduced him to gang life], the kids he had run with before his first arrest,' his lawyer, Steven Greenberg, wrote. 'They became his crew - for a price - and gave him the self-esteem he had always craved and had never had.

He also bought cars, including a $90,000 black Mercedes convertible, an approximately $60,000 2011 Range Rover, and an $80,000 Porsche Panamera. According to the Tribune, he spent 'millions' of dollars on luxury vehicles.

After the lawyers took half the settlement, Jimenez had little left of his award after what he spent.

Meanwhile, the face-tatted gang was flexing its muscle in the neighborhood, driving around, flashing guns and cash, making threats to random people on the street, getting into the drug business, and posting videos threatening rivals and police.

His girlfriend and mother of his two children, Jessica Taylor, says Jimenez has 'trust issues' relating to his time in prison

Jimenez also had two children with his girlfriend, Jessica Taylor.

Prosecutors said the gang 'promotes an atmosphere of terror that devastates neighborhoods and leads only to increasingly longer prison terms, or death,' and that they had a 'feudal means of self-governance.'

It all came to a head on the morning of August 2015, when Jimenez and member Jose Roman drove around in the black convertible Mercedes, looking for a victim.

The two had guns, including Jimenez's custom-plated pistol and Roman's .22-caliber Mossberg semiautomatic rifle, Gucci bags full of ammunition, and an iPhone to record it all. Their soundtrack of choice was opera music.

As the video showed, when the pair ran across Earl Casteel, 33, a former member of the gang and a friend, he greeted them warmly.

'What's up, folks?' Casteel asks when the car pulls up.

'Why shouldn't I blast you right now?' Jimenez says, according to transcript of the video.

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Casteel would need steel reinforcements in his legs and months of physical therapy. He sued the Jimenez estate and won a $6.3 million judgment in December. His lawyer is trying to track down whatever assets Jimenez has left.

Although Jimenez's lawyer argued that he should receive the minimum in prison for his crime since he'd already spent 16 years behind bars for a crime he didn't commit, the judge sentenced him to nine years, slightly less than the maximum of ten.

In a federal filing, prosecutors summed up the strange story this way: '[Jimenez] could have used this money in any number of ways - to assist friends and family, contribute to the community, sponsor others wrongfully convicted or simply live in comfort for the rest of his natural life - instead he chose to build a gang.'